Shady Side MD Real Estate & Homes for Sale

This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy, open feel. Charming cottage-style windows fill the space with natural light, and LVP flooring flows seamlessly through the living room, kitchen, and wide hallway to the bedrooms. The kitchen features oil rubbed bronze fixtures, soft-close cabinets, granite countertops, and a center island with overhang for stools, plus space for a dining table. There is also potential for a deck off the back of the home, perfect for outdoor living. The main level includes two secondary bedrooms and a spacious owners suite. The secondary bedrooms feature custom molding, decorative wall trims, and stylish paint finishes-one accented with decorative peelable wallpaper-and share a hall bath with granite vanity and shower/tub combo. Enjoy views of the wooded landscape from the owners suite, complete with two closets and a distinctive en-suite bath featuring dual sinks, granite countertops, a walk-in shower, custom wall trim accents, and removable wall covering. The lower level provides a versatile living space, including a spacious recreation room with sliding glass doors to the backyard, a flexible 4th bedroom ideal for guests or an in-home office, and an additional full bath with granite vanity and shower/tub combo. Raised garden beds just outside in the backyard and alongside the home are ideal for growing vegetables and flowers.

Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on the Bay. Just steps from the water and community marina, this delightful Cape Cod captures the relaxed essence of coastal cottage living. Situated on a spacious corner lot, the property comes alive in the spring with mature plantings and established landscaping that surround the home, creating a colorful and inviting setting throughout the seasons. A brand-new roof (2025) offers peace of mind, while newer appliances and fresh interior paint provide a bright, refreshed feel inside. With 4 bedrooms and 3 full baths, this home offers flexible living arrangements to fit a variety of lifestyles. The main level features two bedrooms, a full bath, and convenient laundry-ideal for easy one-level living or welcoming guests. Upstairs, a versatile flex space is perfect for a home office, reading nook, or creative studio. Cedarhurst on the Bay enhances any lifestyle with its community marina, community center, and neighborhood playground, offering wonderful spaces to gather, relax, and enjoy this coastal setting. Charming, inviting, and full of potential, this cottage-inspired retreat is ready for its next chapter by the water.

Stunning 4BR / 2.5BA home at 4951 Dogwood Street, Shady Side - freshly painted,hardwood floors have been polished and carpets professionally cleaned, bright, open living with a NEW 2025 Aloha Pool private pool, pool-style is Chesapeake Atlantic 24x54 w/ Liner pad and Styrofoam Covering, NEW oversized deck 22 x 23 ideal for entertaining, 6â??ft privacy fence, and a 2â??car garage. Spacious primary suite, 3 other large bedrooms, abundant storage and finished living spaces create a turnkey Chesapeake retreat. Total house SQ Ft 2586.Enjoy direct access to swimming, crabbing, fishing, water skiing and kayaking - plus a community tot lot and more outdoor amenities. Located in a friendly waterfront community known for boating and relaxed smallâ??town charm. Easy access to Rt. 2/4 and MDâ??214 - roughly 30-45 minutes to Annapolis, and about 45 minutes to Washington, DC, Baltimore and Northern Virginia depending on traffic. Local dining includes waterfront crab houses, casual cafés and family restaurants in Shady Side, Deale and nearby Annapolis.Come home to peaceful scenery and the quiet of South County living - the perfect retreat after a long day. Schedule your showing today. This home won't be on the market long!

Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on the Bay. Just steps from the water and community marina, this delightful Cape Cod captures the relaxed essence of coastal cottage living. Situated on a spacious corner lot, the property comes alive in the spring with mature plantings and established landscaping that surround the home, creating a colorful and inviting setting throughout the seasons. A brand-new roof (2025) offers peace of mind, while newer appliances and fresh interior paint provide a bright, refreshed feel inside. With 4 bedrooms and 3 full baths, this home offers flexible living arrangements to fit a variety of lifestyles. The main level features two bedrooms, a full bath, and convenient laundry - ideal for easy one-level living or welcoming guests. Upstairs, a versatile flex space is perfect for a home office, reading nook, or creative studio. Cedarhurst on the Bay enhances any lifestyle with its community marina, community center, and neighborhood playground, offering wonderful spaces to gather, relax, and enjoy this coastal setting. Charming, inviting, and full of potential, this cottage-inspired retreat is ready for its next chapter by the water.

This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy, open feel. Charming cottage-style windows fill the space with natural light, and LVP flooring flows seamlessly through the living room, kitchen, and wide hallway to the bedrooms. The kitchen features oil rubbed bronze fixtures, soft-close cabinets, granite countertops, and a center island with overhang for stools, plus space for a dining table. There is also potential for a deck off the back of the home, perfect for outdoor living. The main level includes two secondary bedrooms and a spacious owner's suite. The secondary bedrooms feature custom molding, decorative wall trims, and stylish paint finishes - one accented with decorative peelable wallpaper - and share a hall bath with granite vanity and shower/tub combo. Enjoy views of the wooded landscape from the owner's suite, complete with two closets and a distinctive en-suite bath featuring dual sinks, granite countertops, a walk-in shower, custom wall trim accents, and removable wall covering. The lower level provides a versatile living space, including a spacious recreation room with sliding glass doors to the backyard, a flexible 4th bedroom ideal for guests or an in-home office, and an additional full bath with granite vanity and shower/tub combo. Raised garden beds just outside in the backyard and alongside the home are ideal for growing vegetables and flowers.

Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub and shower combination. The bright kitchen shines with white cabinetry and brand new, never used stainless steel appliances, giving it a clean, fresh feel. The living room opens to the fenced backyard and patio through a sliding glass door, inviting easy indoor and outdoor living. Just one step down from the living room is a private office with double doors, its own half bath, and access to the laundry and utility room, offering flexible space for working from home, hobbies, or guests. Outside, the circular driveway provides generous parking, and the backyard shed adds convenient storage for beach chairs, bikes, and lawn equipment. BOAT SLIPS AVAILABLE

Stunning 4BR / 2.5BA home at 4951 Dogwood Street, Shady Side - freshly painted,hardwood floors have been polished and carpets professionally cleaned, bright, open living with a NEW 2025 Aloha Pool private pool, pool-style is Chesapeake Atlantic 24x54 w/ Liner pad and Styrofoam Covering, NEW oversized deck 22 x 23 ideal for entertaining, 6-ft privacy fence, and a 2-car garage. Spacious primary suite, 3 other large bedrooms, abundant storage and finished living spaces create a turnkey Chesapeake retreat. Total house SQ Ft 2586.Enjoy direct access to swimming, crabbing, fishing, water skiing and kayaking - plus a community tot lot and more outdoor amenities. Located in a friendly waterfront community known for boating and relaxed small-town charm. Easy access to Rt. 2/4 and MD-214 - roughly 30-45 minutes to Annapolis, and about 45 minutes to Washington, DC, Baltimore and Northern Virginia depending on traffic. Local dining includes waterfront crab houses, casual caf s and family restaurants in Shady Side, Deale and nearby Annapolis.Come home to peaceful scenery and the quiet of South County living - the perfect retreat after a long day. Schedule your showing today. This home won't be on the market long!

THIS IS A TO BE BUILT HOME

THIS IS A TO BE BUILT HOME

Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub and shower combination. The bright kitchen shines with white cabinetry and brand new, never used stainless steel appliances, giving it a clean, fresh feel. The living room opens to the fenced backyard and patio through a sliding glass door, inviting easy indoor and outdoor living. Just one step down from the living room is a private office with double doors, its own half bath, and access to the laundry and utility room, offering flexible space for working from home, hobbies, or guests. Outside, the circular driveway provides generous parking, and the backyard shed adds convenient storage for beach chairs, bikes, and lawn equipment. BOAT SLIPS AVAILABLE

HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their latest Monroe model located in water privilege community offering community beach, pier, boat ramp, playground, slips, and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded features, and there is still the opportunity to make your personal selections to suit your needs and make this home yours! Some of the standard features will include 9 ceilings on the main level, luxury vinyl plank flooring, stainless steel appliances, large eat-in kitchen with island, 42� designer Craftsman cabinets, large owners suite with luxury bath, upper-level laundry room, and plenty more! 2 car garage!. Construction to perm financing is available. Photos are illustration purposes only. Late summer 2026 delivery Must use builder contract - buyer responsible for 100% transfer taxes**. Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary. $10,000 closing assistance with preferred lender. Completed model located at mdca2024952.

HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their latest Monroe model located in water privilege community offering community beach, pier, boat ramp, playground, slips, and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded features, and there is still the opportunity to make your personal selections to suit your needs and make this home yours! Some of the standard features will include 9' ceilings on the main level, luxury vinyl plank flooring, stainless steel appliances, large eat-in kitchen with island, 42 designer Craftsman cabinets, large owner's suite with luxury bath, upper-level laundry room, and plenty more! 2 car garage!. Construction to perm financing is available. Photos are illustration purposes only. Late summer 2026 delivery Must use builder contract - buyer responsible for 100% transfer taxes**. Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary. $10,000 closing assistance with preferred lender. Completed model located at mdca2024952.

Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home. The primary heating system is oil-fired radiator heat, complemented by a ductless mini-split system on the main level. A versatile bonus room on the main floor may serve as a third bedroom or home office. Hardwood floors run throughout the home (currently under area carpet), and newer windows. The home is being sold as is, and most contents will convey with the sale.

Estate sale handled by an attorney. This well-loved home has been in the same family since 1953 and is now ready for its next chapter. Offering generous living space and abundant potential, this property is ideal for buyers looking to build sweat equity and restore its original charm. Situated on a large lot, the sale also includes an additional 25' x 100' parcel located to the right of the home. The primary heating system is oil-fired radiator heat, complemented by a ductless mini-split system on the main level. A versatile bonus room on the main floor may serve as a third bedroom or home office. Hardwood floors run throughout the home (currently under area carpet), and newer windows. The home is being sold as is, and most contents will convey with the sale.

4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of Ma2 zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of Ma2 zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space - thoughtfully laid out to balance comfort and function. Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed kitchen with stainless appliances and abundant cabinetry flows seamlessly into living areas perfect for both relaxing evenings and entertaining guests. The home also boasts central a cozy fireplace, and an attached garage for convenience. Retreat to the spacious first floor primary suite featuring its own full bath with jetted tub and separate shower. The second floor encompasses two additional bedrooms and and full bath providing flexibility for family, guests, or a home office. Outdoor spaces include a recently built screened in porch with composite decking and a private fenced backyard - ideal for summer barbecues, gardening, or simply enjoying Marylands beautiful seasons. Situated on a well-sized 7,500+ sq ft lot in a welcoming neighborhood, youre minutes from local schools, Chesapeake Bay waterfront attractions, marinas, dining, and community amenities. Embrace serene suburban living with easy access to Annapolis and the greater Baltimore/Washington region.

This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room with sliding door leading to a stunning sunroom and adjacent deck-perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms and a second full bath provide plenty of space for family or guests. Additional highlights include a two-car garage, a two-car carport, a large storage shed, and a handicap-accessible ramp. Situated on a level, usable one-acre lot, this home combines comfort, functionality, and outdoor space in a peaceful setting. No covenants or restrictions.

This spacious and well-maintained home offers the ease of one-level living at it's best. The modern kitchen opens to a cozy family room with sliding door leading to a stunning sunroom and adjacent deck - perfect for relaxing or entertaining. Enjoy formal spaces with both a living room and dining room, along with a generous primary suite complete with a private full bath. Two additional bedrooms and a second full bath provide plenty of space for family or guests. Additional highlights include a two-car garage, a two-car carport, a large storage shed, and a handicap-accessible ramp. Situated on a level, usable one-acre lot, this home combines comfort, functionality, and outdoor space in a peaceful setting. No covenants or restrictions.

Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space - thoughtfully laid out to balance comfort and function. Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed kitchen with stainless appliances and abundant cabinetry flows seamlessly into living areas perfect for both relaxing evenings and entertaining guests. The home also boasts central a cozy fireplace, and an attached garage for convenience. Retreat to the spacious first floor primary suite featuring its own full bath with jetted tub and separate shower. The second floor encompasses two additional bedrooms and and full bath providing flexibility for family, guests, or a home office. Outdoor spaces include a recently built screened in porch with composite decking and a private fenced backyard - ideal for summer barbecues, gardening, or simply enjoying Maryland's beautiful seasons. Situated on a well-sized 7,500+ sq ft lot in a welcoming neighborhood, you're minutes from local schools, Chesapeake Bay waterfront attractions, marinas, dining, and community amenities. Embrace serene suburban living with easy access to Annapolis and the greater Baltimore/Washington region.

Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife-waterfowl, deer, eagles, and more-all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is even within sight. The home features a relaxing screened porch, a spacious kitchen that flows into a cozy living area with a wood stove-perfect for chilly evenings. The main level includes a bedroom and full bath, plus an additional room ideal for an office or second living space, also with a wood stove. Upstairs, the primary bedroom offers breathtaking water views, accompanied by another bedroom and a full bath. A barn/stable on the property makes it ideal for horses or a home-based business with office space. This is truly a one-of-a-kind property-peaceful, picturesque, and full of potential. Come see it for yourself.

Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife - waterfowl, deer, eagles, and more - all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is even within sight. The home features a relaxing screened porch, a spacious kitchen that flows into a cozy living area with a wood stove - perfect for chilly evenings. The main level includes a bedroom and full bath, plus an additional room ideal for an office or second living space, also with a wood stove. Upstairs, the primary bedroom offers breathtaking water views, accompanied by another bedroom and a full bath. A barn/stable on the property makes it ideal for horses or a home-based business with office space. This is truly a one-of-a-kind property - peaceful, picturesque, and full of potential. Come see it for yourself.

Peaceful Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty-with low maintenance. Just a short walk to the bay front, youll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates-roof, HVAC, water softener, and well pump-all done within the last 3 years-mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage and a roomy driveway (with space for a boat or guests), and surrounding greenery make outdoor living simple and serene. Plus, the neighboring nature reserve means no new development next door-ever. If youre ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

Peaceful Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal opportunity for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural beauty - with low maintenance. Just a short walk to the bay front, you'll love starting your mornings with coastal breezes and winding down with sunset walks to the community pier. Inside, enjoy a warm and inviting open layout, complete with a cozy wood stove and a splash of personality from the bright red front door. Major updates - roof, HVAC, water softener, and well pump - all done within the last 3 years - mean you can move in and relax from day one. The manageable yard has 2 sheds for extra storage and a roomy driveway (with space for a boat or guests), and surrounding greenery make outdoor living simple and serene. Plus, the neighboring nature reserve means no new development next door - ever. If you're ready to downsize to comfort, convenience, and coastal charm, this is the home for you.

To be built by Whitehall Building & Co., Annapolis' leading luxury waterfront builder. Set within the sought-after Columbia Beach community, this coastal-style home captures the best of Chesapeake Bay living with panoramic views and the rare protection of a cove-front setting. With Whitehall, the path to building is refreshingly simple. Their step-by-step process begins with a complimentary consultation and clear timeline that removes the guesswork so you can enjoy the creative side of designing your dream home. Every stage is transparent and organized, from selections to finishes, with a dedicated team guiding you the entire way. Visit their website for more info about Whitehall! Building a custom home may take time, but with Whitehall it never feels complicated. You can relax knowing the details are handled and the outcome will be worth the journey. Enjoy the lifestyle that follows: a thoughtfully designed waterfront home built around how you truly live, with access to community amenities including a boat launch, pier, tennis and basketball courts, and playgrounds, all just a short drive from Annapolis, DC, and Baltimore.